1. Round | 10/08/2019 | Linfield FC | - | Institute FC Drumahoe | 3:1 | ||||
2. Round | 13/08/2019 | Institute FC Drumahoe | - | Dungannon Swifts | 2:3 | ||||
3. Round | 17/08/2019 | Institute FC Drumahoe | - | Carrick Rangers | 0:2 | ||||
4. Round | 24/08/2019 | Coleraine FC | - | Institute FC Drumahoe | 0:0 | ||||
5. Round | 02/09/2019 | Glentoran FC | - | Institute FC Drumahoe | 4:0 | ||||
6. Round | 07/09/2019 | Institute FC Drumahoe | - | Crusaders FC | 0:6 | ||||
9. Round | 28/09/2019 | Warrenpoint Town | - | Institute FC Drumahoe | 1:3 | ||||
10. Round | 05/10/2019 | Institute FC Drumahoe | - | Ballymena United | 1:1 | ||||
12. Round | 19/10/2019 | Institute FC Drumahoe | - | Cliftonville FC | 0:3 | ||||
13. Round | 26/10/2019 | Larne FC | - | Institute FC Drumahoe | 1:1 |